Triethylamine → 4-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamide

HRID 7066

Reaction equation

HRID 7066 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14](I)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20].[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)#[CH:22].C(N(CC)CC)C>[Cu]I.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(#N)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:22]#[C:21][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:13]=2)=[O:10])=[CH:4][C:3]=1[O:19][CH3:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 10821PhenylacetyleneHCID 120966604-hydroxy-N-(3-iodophenyl)-3-methoxyphenylacetamide

Product 1

HCID 220196124-hydroxy-3-methoxy-N-[3-(2-phenylethynyl)phenyl]-phenylacetamideYield 77.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of Intermediate 1 (2.5 g), ethynylbenzene (800 mg), copper (I) iodide (124 mg), bis(triphenylphosphine)palladium (II) dichloride (1.37 g), triethylamine (19.0 g) and acetonitrile (20 ml) is heated with stirring at 50° C. under argon atmosphere. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate) to give the desired compound (1.8 g).

Workup

  1. temperatureis heated
  2. customThe solvent is evaporated under reduced pressure
  3. customthe residue is purified by silica gel column chromatography (eluent: gradient from 0% to 100% hexane/ethyl acetate)

Sources & evidence

ORD record
ord-144fec4e7c764ed7b72601061fc955a2
Source dataset
uspto-grants-2006_08
Patent number
US07084176B2

Linked notes

Loading…